Tin-free three-component coupling reaction of aryl halides, norbornadiene (or norbornene), and alkynols using a palladium catalyst.
TLDR
In this paper, a Pd/Cu catalyzed three-component ternary coupling reaction of aryl halides, norbornadiene, and alkynols in toluene at 100 °C in the presence of 5.5 M NaOH as a base and benzyltriethylammonium chloride as a phase transfer catalyst.Abstract:
Good-to-excellent yields of 2,3-Disubstituted norbornenes (or norbornanes) were obtained using a Pd/Cu catalyzed three-component ternary coupling reaction of aryl halides, norbornadiene (or norbornene), and alkynols in toluene at 100 °C in the presence of 5.5 M NaOH as a base and benzyltriethylammonium chloride as a phase transfer catalyst. The results of experiments using various aromatic halides suggest that the ternary coupling reaction is promoted by bromide.read more
Citations
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Enantioselective Synthesis of Indanols from tert‐Cyclobutanols Using a Rhodium‐Catalyzed C ? C/C ? H Activation Sequence
TL;DR: Tert.-Cyclobutanols were activated through an enantioselective rhodium(I)-catalyzed insertion into the C-C bond leading to arylrhodium species that are converted to indanol derivs.
Journal ArticleDOI
Insertions of Ketones and Nitriles into Organorhodium(I) Complexes and β-Hydrocarbyl Eliminations from Rhodium(I) Alkoxo and Iminyl Complexes
Pinjing Zhao,John F. Hartwig +1 more
TL;DR: A series of tris(triethylphosphine)-ligated organorhodium(I) complexes were prepared, and their reactions with electron-poor arylnitriles and diarylketones were studied as discussed by the authors.
Journal ArticleDOI
Palladium-Catalyzed 1,2-Addition of Organic Halides and Terminal Alkynes to 7-Oxabenzonorbornadiene : An Efficient Route to Polyaromatic Hydrocarbons
TL;DR: In this paper, a three-component coupling reaction of organic halides with oxabicyclic alkenes and terminal alkynes was catalyzed by a palladium complex and a phase-transfer agent in the presence of aqueous NaOH.
Journal ArticleDOI
Palladium-catalyzed three-component coupling reaction of organic halides, norbornadiene and terminal alkynes
TL;DR: A three-component coupling reaction of organic halides, including aryl halide, methyl iodine, alkenyl iodine and bromoalkynes, with norbornadiene and terminal alkynes catalyzed by a palladium complex and a phase transfer agent in the presence of aqueous NaOH gave 5,6-disubstituted norbornene derivatives in good yields.
References
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Toxicity of dibutyltin, tributyltin and other organotin compounds to humans and to experimental animals.
TL;DR: Tributyltin oxide produced mutations in Chinese hamster ovary cells, increased the incidence of micronuclei in the erythrocytes of exposed male BALB/c mice, and was highly embryotoxic in vitro.
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A short route to dehydro [12] annulenes.
Chanh Huynh,Gérard Linstrumelle +1 more
TL;DR: In this paper, a novel synthesis of annutenes from 1,2-dibromobenzene is based on selective Pd(0)-Cu(1) coupling reactions of aryl and vinyl halides with tenninal acetylenes.
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A new catalytic reaction involving oxidative addition of iodotrimethylsilane (Me3SiI) to palladium(0). Synthesis of stereodefined enynes by the coupling of Me3SiI, acetylenes, and acetylenic tin reagents
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A new palladium catalyzed synthesis of ,-2,3-diarylsubstituted bicyclo[2.2.1]heptanes or bicyclo [2.2.1] hept-2-enes
TL;DR: The bicycloheptanes or bicyclo-heptenes as discussed by the authors were obtained by oxidative addition of aryl bromides to palladium(0), followed by double bond insertion and coupling with a phenyl group of tetraphenyl borate anion.